(S)-Tert-butyl 3-(azidomethyl)piperidine-1-carboxylate → tert-Butyl (3R)-3-(aminomethyl)piperidine-1-carboxylate

HRID 1478605Notes

Reaction equation

HRID 1478605 reaction equation
[N:1]([CH2:4][C@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][C@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1

Participants

4

Reactant 1

HCID 10083012(S)-Tert-butyl 3-(azidomethyl)piperidine-1-carboxylate

Product 1

HCID 1502023tert-Butyl (3R)-3-(aminomethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-tert-butyl 3-(azidomethyl)piperidine-1-carboxylate (5.38 g, 22.40 mmol) was dissolved in MeOH (50 ml), and then Pd/C (5% mol) was added, followed by stirring at room temperature under H2 (gas) for 9 hours. After the completion of the reaction, the reaction mixture was filtered through celite, followed by filtration and concentration under reduced pressure, and then the next reaction was advanced without purification.

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe reaction mixture was filtered through celite
  3. filtrationfollowed by filtration and concentration under reduced pressure
  4. customthe next reaction
  5. customwas advanced without purification

Sources & evidence

ORD record
ord-f6fc61fefd43412c92d12202819e8678
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

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